


Oh The Tangled Web We Weave

by lunar47



Category: Community (TV)
Genre: F/M, Fluff and Angst, Frottage, Mutual Masturbation, Non-Consensual Voyeurism, Not Canon Compliant, Original Character(s), Porn With Plot, Power Play, Voyeurism, but with feelings, just like really filthy smut, minor Annie/OC, minor Jeff/OC
Language: English
Status: Completed
Published: 2015-08-29
Updated: 2015-08-29
Packaged: 2018-04-17 22:19:24
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,981
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4683452
Author URL: https://archiveofourown.org/users/lunar47/pseuds/lunar47
Summary: <blockquote class="userstuff">
              <p>Annie definitely doesn’t have a crush on Jeff. She’s moved on. They’re friends. Right? Platonic friends? Then why does an argument end in the most obscene heart stopping sex ever in the alleyway behind a bar on Annie’s 21st birthday? And why must the outcome always be so bittersweet?</p>
            </blockquote>





	Oh The Tangled Web We Weave

**Author's Note:**

  * For [alissabobissa](https://archiveofourown.org/users/alissabobissa/gifts).



> So I began writing this sometime after the episode with Troy's 21st birthday then put it aside for years. I just finished it today. So just ignore canon after that episode. Also my prompt for this was sex outdoors and destructive relationships for liketrains on livejournal.

The shiny red vinyl felt slightly sticky to Annie’s touch. She focused on that instead of the conversation and laughter bouncing back and forth across the large, rounded, corner booth. It was her 21st birthday and apparently they were tempting fate by going back to the same bar that had caused so much tension at Troy’s 21st. It wasn’t her idea; she had just wanted a nice dinner, but the group insisted on trying the bar again. When she had looked at Abed for support that sequels were never a good thing he cocked his head in thought and then went on to describe how their paintball sequel exceeded their original game in every way. 

So there she sat, unhappily squished between Britta and Annie's own boyfriend Paul. Paul was a new addition to Annie’s life. He was sweet and kind and a little shy. He sat next to her in her sociology class and according to him it had taken weeks to get up the nerve to ask her out. Two months later and they were officially a couple. He wasn’t actually a member of the group but he had tagged along to a few of their outings. 

Paul moved his hand to stroke the bare skin just below the hem of her skirt and she flinched. Smiling apologetically he folded his hands back onto his lap.

“I’m sorry. I’m just not feeling too well.” Annie explained. 

“We can go if you like? Do you want me to take you home?” Paul was always considerate. From the very first day she had met him and he gave up his seat in the front row of class because that was her preferred spot.

“No, of course not. Everyone seems to be having so much fun.” She gave a tired smile.

And they were having fun. Especially Jeff it seemed. Besides herself and Shirley, who had stuck the kids with a babysitter and brought Andre, Jeff was the only one to bring a date. Apparently she was the new girl in his life. Probably short lived given his still nonexistent attention span when it came to women. There was only so much that could change. 

Annie glanced over at Jeff and Kristi (Kelly?) and her stomach turned. Kristi, yeah it was definitely Kristi, had her hand on his chest as she whispered something in his ear. It was obviously something amusing given how Jeff chuckled and pulled her closer. 

She didn’t know why it bothered her. It’s not like Jeff and Annie were dating or had ever dated. She was over him and whatever romantic feelings she may have had at one time were gone. They were only good friends now. That much had been decided upon during an uncomfortable but much needed discussion over the summer. She flat out refused to call this feeling jealousy. 

All the same she needed out. She felt like she was suffocating. Excusing herself from the booth she made as if to go to the bathroom. But when she saw that no one was looking she double backed, avoiding the group’s table, and exited out the front door. 

The night sky was cloudy and moist from the rain that had fallen that evening. The light from the sodium vapor street lamps cast an eerie orange glow on everything. She shivered in the cold as she moved past some rowdy people and into the secluded alleyway between the bar and the dry cleaners next door. It wasn’t the best idea to be here alone given how many crime shows depicted murdered girls in dingy dumpsters but it was away from the group (read: Jeff). 

She didn’t know what to do about him, how to feel about him. Annie leaned against the brick wall and kicked it with her heel. She was a big ball of twisty emotion and she hated that. She would blame Jeff. It made everything easier in her mind, took the responsibility off her shoulders.

“Need your umbrella?” She jumped when she heard Jeff’s voice from the shadows. He approached her nonchalantly, twirling the umbrella in his hand.

“How did you know I was out here?” Annie was half curious half accusing him of something nefarious.

His lip quirked in amusement, “I saw you circle back to the door when you faked going to the restroom.” Jeff’s response lacked any undertone and she relaxed.

“Oh.” She sighed and reached for the umbrella. “I just needed some air.”

“So you came to a dirty alleyway to do it.”

She shrugged. “It was quiet. The bouncer was dealing with a bunch of drunken frat guys at the door.”

“Yeah and that makes the alley a superior choice.” His reply was laced with sarcasm. 

“Why are you even here Jeff?” Annie’s ire was once again stoked.

“Maybe I wanted to see if my friend was alright.” He took a step towards her.

“Friend?” Was friend really the right word for whatever nebulous relationship they had?

“Are we back to this shit again?” Jeff acted as if he couldn’t believe Annie would stoop so low.

“Excuse me?”

“Were you jealous of Kristi and me?” In her opinion his question seemed to come out of left field.

“No, of course not. I have a boyfriend, you know.” Annie replied defensively.

“I do know,” His face crowded hers. “So why isn’t he out here and I am?”

It was at this point that Annie realized that Jeff was definitely in her personal bubble, leering over her, his face so close she could feel his exhale on her lips. She didn't want to think about that…his mouth, her lips. She had a boyfriend, remember.

She swallowed roughly and she could tell that Jeff didn't miss the furtive glance she gave to his slightly chapped lips or the way her tongue peaked out and ran quickly over her own smooth ones. 

Oh she was in trouble. Her heart sped up and she could feel it pounding against her chest. An awful tightening wound its way into her abdomen…or maybe it was a little lower. She unconsciously squeezed her thighs together.

What was she thinking? Annie huffed and jut her chin out defiantly, “I'm going back inside.” She wouldn't be a slave to her hormones.

Jeff stuck his hand above her head, palm hard against the brick wall. He had essentially blocked her exit and leaned into her further. His voice was low and dangerous, “Oh are you now? Is that what you really want Annie?”

She struggled to inhale, conflicted as she was. Her mind told her to be a good girl, go back inside, sit next to Paul, and laugh at his corny jokes. 

But her body wanted to do very bad things.

Jeff got closer, till his mouth ghosted her ear and he spoke softly, “I want to fuck you Annie.”

She came undone. Annie tossed the umbrella away and turned her mouth towards Jeff’s face. She slid it along his cheek until she found his lips for a searing kiss. Annie wrapped her arms around his neck as Jeff’s hands reached for her bottom. He bunched up the fabric of her skirt in his hands and she moaned around his tongue. 

Jeff pushed her further into the brick wall. His fingers grabbed at her underwear intending to pull them off or aside, his ultimate goal to lift her up and wrap her legs around his waist. He wanted to take her against the wall. Annie had other ideas.

“No, like this.” She took her own hand and pulled up the front of her skirt where it had fallen. Then she stuck her fingers down her underwear and began to massage her clit. Annie closed her eyes and leaned her head back on the building. 

When she opened them she saw that Jeff’s eyes were heavy lidded and a little glazed over. He bent down to kiss the side of her neck moving up to fiercely take her lips. He sucked the bottom one into his mouth and bit it gently. Annie let out what she could only describe as a low growl. 

She removed her hand from her underwear and reached for Jeff's hand to replace her own. He took the hint and rubbed his thumb against her sensitive spot. She keened softly and fell forward onto him. Sensations were building. She wanted this. Had to have this from him.

“I need to be inside you,” Jeff groaned while he continued to stroke her.

“No,” Was her simple reply. 

So he did the next best thing. With his thumb on her clit he curled two of his fingers inside her. Annie gasped and gripped her hands tightly in his shirt.

Suddenly she let go and fumbled with the button and zipper to Jeff’s jeans. She pulled out his cock to find him already hard.

“I thought...you weren't...going to let me fuck you.” Jeff was having a little trouble getting out a coherent sentence with Annie’s hand squeezing gently around his member.

“I'm not.”

“Then what the hell are we doing, Annie.” His hand had stopped his ministrations.

“Something I can live with,” she licked her palm while looking him straight in the eyes and returned her now wet fingers to his erection. “Now keep going.”

So he did. And Annie learned that she was a quiet lover. She made the occasional moan and breathy exhalation but mostly she stayed silent. Jeff on the contrary had one hand bringing her to what surely would be one of her most memorable orgasms and he had his other hand wrapped tightly in her long hair. He uttered absolutely filthy things in her ear and it only made her more aroused. Her sex throbbed and she felt so close to coming apart completely.

She tried to focus on Jeff. On running her slick hand up and down his shaft. She wasn't surprised by the length or thickness. She'd heard enough boasting conversations between the boys in their group to roll her eyes. But to see it in person almost made her want to forget her convictions, just give in and let Jeff take her right in that terrible alley. But to do that would be crossing a line she couldn't come back from as little sense as that made.

In the distance she heard the crack of a glass bottle breaking on cement and a lewd whistle that could only be meant for them. She paused briefly, turning her head toward the sound.

“Forget about it,” and Jeff jerked her head back by her hair to meet his own, their lips crashing in a messy kiss. He changed the angle of his thumb on her clit and she tensed. That did it, her orgasm coming over her in waves. She unintentionally squeezed Jeff's cock hard but she didn't have the words to apologize. The wall held her up, barely, and Jeff’s arms were doing the rest. 

“Good?” His question was almost arrogant as was the smirk on his face.

She sighed in contentment and watched as he pulled his hand out of her underwear. Annie could see that his fingers were wet and that made her feel unspeakable things. 

She'd let go of Jeff in the wake of her climax but now he took himself in hand and he was stroking himself. An expert in knowing what he liked of course. She had been a mere amateur. She pulled down her underwear to her knees and grabbed his ass bringing him closer.

“Not inside, do you understand?” Annie felt powerful giving commands to Jeff, expecting him to just follow.

He nodded roughly and fit himself between her legs, the height difference making things a bit awkward but he didn't seem to care. He lifted her up a bit till she was on her tip toes and then he was rutting against her. It was so animalistic. So obscene. He rubbed against her already swollen and sensitive clit. 

“Oh, fuck Annie. The things you do to me.” 

She could say the exact same thing about Jeff. 

His breathing grew ragged and finally he grunted. His cock slipped from her thighs and she felt wetness pool between them. Jeff held her close. It was the most intimate moment she had ever shared with him and yet she also felt a certain distance from what was going on. This had been…she didn't know what to call it exactly. Sex in a way, she guessed. 

Suddenly she was overwhelmed. Overwhelmed by Jeff's hulking form, his scent all over body, the lingering feeling of arousal and satiation. What had they done? Given in to a momentary weakness…on both their parts.

She shoved Jeff away from her, not roughly and stepped closer to the alley entrance. Annie pulled up her underwear and smoothed down her skirt. The moisture she felt was an uncomfortable reminder of their activities.

Jeff seemed stunned for a moment, his penis still hanging out in the open, before he quickly put himself away and straightened himself out. They stood staring at one another. It was like he was waiting for her to return to typical Annie.

She blinked, took in a steadying breath and then she was herself again. “What am I supposed to say when we walk back in there?” She half yelled at him.” That we had sex in some dirty alley?” Annie paced in front of him. “Oh my god, Paul. He’ll be heartbroken.” The words came out as if by rote but she didn’t feel their weight.

“Then don’t tell him. Or you could always blame it on the alcohol.”

“I’m perfectly sober I’ll have you know. I was drinking ginger ale.” There were no excuses for her actions. Just lust and Jeff. Yes…Jeff in close proximity. She had weaknesses and she didn’t want to admit that the former lawyer was one of them. 

Annie placed her hands on her hips, rocked back and forth on her heels and when she grew too agitated she crossed her arms in front of her. A purely defensive gesture.

She cast her eyes downward and spoke honestly, “I don’t know what to do now.”

Jeff walked up to her and with a fair amount of hesitation placed his hands on her arms. “We didn’t do anything wrong.”

“Didn’t do anything wrong, Jeff? Of course we did. I have Paul. You have Kelly.”

“Kristi.”

“Exactly. It was morally wrong. Unethical. This could hurt people.” Annie’s voice broke a little at the thought. 

“It was inevitable, Annie. The two of us. This was always going to happen. It was just a matter of time," Jeff paused. “A time bomb and we literally just went off.” He squeezed her arms to emphasize his point. “When you say this was morally wrong I don’t think this is about Paul. I think this is about denying yourself something that you’ve wanted. Fantasized about and didn’t think you could have. You want to be the good girl, the straight-A student, but there’s more to you than that. You’re complicated and I like that.”

“You told me we should be just friends though. We agreed...” Annie trailed off. That summer conversation in the Greendale Happy Valley Café over milkshakes was clear in her mind.

“Maybe you deserved better than some washed up ex-lawyer going to a half rate community college. Maybe I was trying to do the noble thing for once.”

“What are you trying to say Jeff? That you want me? Want to be with me?” Annie didn’t want to hope.

Jeff brought his hands up to tenderly cup her face. It was a move so gentle that it lied in stark contrast to their previous actions in the alley. “And if I did? Would that be so bad?”

Annie reached up to touch his wrist, “What about Paul?”

“Forget about him. You’ve been going out with him for what? All of five minutes. Is it serious? Does it even compare to what we have?”

“No it doesn’t remotely compare.” She acknowledged softly. Annie should have felt guilt. And maybe she felt a little way down deep. But she had the chance to grasp something she really wanted, not something she settled for.

She smiled and tears, maybe happy tears, welled up in her eyes. “Kiss me.” And he did, slow and sweet. It was everything that friends to lovers should be.

When they parted he lifted his face to press his lips to her forehead. “Take a cab home, Annie. I’ll make your excuses inside. And tomorrow we’ll talk. We’ll get that fancy dinner you really wanted for your birthday. Just the two of us.” He took a step back from her and he was in fine Winger fashion, “Wear that little black number I know every woman has in the back of their closet.”

She rolled her eyes and then admitted with some embarrassment, “Mine has a big red bow on the front.”

“That will be perfect,” Jeff smiled and he looked like he genuinely meant it.

She gathered her abandoned umbrella and they walked to the curb outside the bar. He hailed a cab for her. She watched Jeff from out the window as he likewise watched her from the sidewalk until the car turned the corner down the street.

Reclining against the plush leather seats she reflected on her wild and highly unexpected evening. It had started with an unwanted birthday party at a bar moving on to fairly shameless sex in an alleyway and then a surprisingly heartfelt discussion with Jeff. She’d have to break up with Paul, and soon. But Jeff seemed earnest that he wanted to try things out with her. And she’d take that chance. Because Jeff was worth the heartache in exchange for a chance at true happiness. 

She’d take those odds any day.


End file.
